My classic car usually sits the entire winter in the garage, as I don't drive it in the bad weather. My late fall ritual goes something like this. Make sure all fluids are fresh and topped off, including gas. A bottle of dry gas and fuel stabilizer in the tank, then run the car to make sure the additives have had a chance to circulate through the entire fuel system. The stabilzier in the tank is great but if it doesn't get into the fuel pump and carbs or injectors then they can fill with varnish and goo and get ruined. The car up on blocks if I know it's not going to be moved for the entire time. I have a trickle charger for the battery, so that gets plugged in, but disconnect the battery from the car while it's on charge. Sometimes I throw a box of baking soda in the interior just to keep funky odors from taking hold. Last I hit all the locks and hinges with lithium grease so they don't seize up. Never had to deal with a Chicago winter though, good luck, if you do a few things like these the car should be fine.